EP1884560B1 - Verfahren zur Herstellung von quartären Ammoniumsalzen - Google Patents

Verfahren zur Herstellung von quartären Ammoniumsalzen Download PDF

Info

Publication number
EP1884560B1
EP1884560B1 EP07018604A EP07018604A EP1884560B1 EP 1884560 B1 EP1884560 B1 EP 1884560B1 EP 07018604 A EP07018604 A EP 07018604A EP 07018604 A EP07018604 A EP 07018604A EP 1884560 B1 EP1884560 B1 EP 1884560B1
Authority
EP
European Patent Office
Prior art keywords
group
quaternary ammonium
carbon atoms
fatty acid
same
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP07018604A
Other languages
English (en)
French (fr)
Other versions
EP1884560A2 (de
EP1884560A3 (de
Inventor
Yasuki c/o Kao Corporation OHTAWA
Takeshige c/o Kao Corporation Tomifuji
Akira c/o Kao Corporation Sakaguchi
Tohru c/o Kao Corporation KATOH
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2001065091A external-priority patent/JP4467821B2/ja
Priority claimed from JP2001065090A external-priority patent/JP4514975B2/ja
Priority claimed from JP2001093069A external-priority patent/JP4672164B2/ja
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP1884560A2 publication Critical patent/EP1884560A2/de
Publication of EP1884560A3 publication Critical patent/EP1884560A3/de
Application granted granted Critical
Publication of EP1884560B1 publication Critical patent/EP1884560B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • the present invention relates to a preparation method of quaternary ammonium salt that is desirably used as a softener base agent, quaternary ammonium salt obtained through such a preparation method and a softener composition containing such salt that exhibits superior softness.
  • the fiber-use softener In recent years, most of the products that are commercially available as the fiber-use softener have a composition containing quaternary ammonium salt having two long-chain alkyl groups in each molecule, as typically represented by di(long-chain alkyl) dimethyl ammonium chloride.
  • the quaternary ammonium salt of this type has a problem in which, when its residual substances after use are discharged into the natural field, most of them are accumulated without being subjected to biodegradation.
  • N-methyl-N,N-bis(long-chain alkanoyl oxyethyl)-N-(2-hydroxyethyl) ammonium methylsulfate or the like has been introduced to the market as modified products.
  • this product has better biodegradability.
  • N-methyl-N,N-bis(long-chain alkanoyl oxyethyl)-N-(2-hydroxyethyl) ammonium methylsulfate is prepared by esterifying triethanol amine using a long-chain fatty acid and successively quaternizing this by dimethyl sulfate.
  • the reaction molar ratio of fatty acid to triethanol amine is normally set to 1.8 to 2.1, and in this case, the ratio of diester quaternary salt to the total amount of monoester quaternary salt, diester quaternary salt and triester quaternary salt is 43 to 47 weight %.
  • the reaction molar ratio is set to 1.8 to 2.1 because at this time, the ratio of diester quaternary salt is maximized, and the reaction molar ratio smaller than 1.8 or greater than 2.1 causes a reduction in the ratio of diester quaternary salt, resulting in degradation in the softening performance.
  • the reaction molar ratio is set within 1.8 to 2.1, it is not necessarily possible to provide a sufficient softening property.
  • WO9742279 has disclosed quaternary ammonium salt in which the ratio of diester quaternary salt is not less than 55 weight % with the ratio of triester quaternary salt being set to not more than 25 weight %, and the preparation method thereof. Although this product has an improved softening performance, it has not been a satisfactory product.
  • softener base agents have the di-long-chain alkyl quaternary ammonium salt structure, and with respect to tri-long-chain alkyl quaternary ammonium salt, the application thereof as a softener base agent has not been proposed because of the reasons that more hydrophilic groups exist in comparison with lipophilic groups with insufficient dispersing property to water with the result that the softening performance is not sufficiently exerted.
  • WO 91/01295 relates to a process for preparing quaternary ammonium compounds with an amino ester function by esterifying fatty acids with alkanolamines.
  • the compounds obtained are alkylated wherein an inert solvent such as an aliphatic or aromatic solvent may be used.
  • the objective of the present invention is to provide a method of preparing quaternary ammonium salts which provide a sufficient softening performance.
  • WO01/32813 and JP-A 2001-131871 disclose a mixture of quaternary ammonium salts including 15 to 85 % of a tri-ester-having quaternary ammonium salt, up to 40% of a diester-having quaternary ammonium salt and 15 to 85 of a mono-ester-having quaternary ammonium salt for a for a softener.
  • DE-A 1935499 discloses production of a tri-ester-having quaternary ammonium for softener, in Example 2.
  • the purpose of the present invention is to provide an efficient preparation method of a quaternary ammonium salt that is excellent in softener base agent and have a good biodegradability.
  • the quaternary ammonium salts are represented by the formulae (I), (II) and (III) wherein R 1 , R 2 and R 3 represent a long-chain alkyl or alkenyl group having the total carbon atoms of 8 to 40, which are the same as or different from one another and may be intersected by an ether group, an ester group or an amide group; R 4 represents an alkyl group, an alkenyl group or a hydroxy alkyl group, having 1 to 6 carbon atoms, plural R 4 's being the same as or different from one another; and X - represents an anionic group.
  • the tertiary amines or salts thereof are represented by the following formulae: (V), (VI) or (VII), wherein R 1 , R 2 , R 3 and R 4 are the same as described above.
  • R 1 , R 2 and R 3 are the same as or different from one anther and are preferably groups represented by the following formula (X) or (XI) : wherein, R 8 and R 9 , which are the same as or different from each other, represent an alkylene group having 2 to 6 carbon atoms and R 10 CO represents a residual group resulting from a fatty acid having 8 to 30 carbon atoms from which a hydroxyl group has been excluded.
  • the present invention provides a method for preparing quaternary ammonium salts represented by the above-mentioned formula (I), (II) or (III), comprising reacting a tertiary amine represented by the above-mentioned formula (V), (VI) or (VII) with a quaternizing agent to prepare a quaternary ammonium salt in at least one aprotic solvent selected from compounds represented by the following formula (XII) : R 11 O-(AO)n-R 12 (XII) wherein R 11 and R 12 , which are the same as or different from each other, present alkyl groups, alkenyl groups or acyl groups, each having carbon atoms of 1 to 30, A represents an alkylene group having carbon atoms of 2 to 4, n represents a number of 1 to 40 on the average and n A's may be the same as or different from one another.
  • aprotic solvent selected from compounds represented by the following formula (XII) : R 11 O-(
  • the aprotic solvent is preferably a compound represented by the formula (XII) is more preferably a compound represented by the formula (IV): R 5 COO-(AO)m-R 6 (IV) wherein, R 5 , R 6 , A and mare defined as the same as described above.
  • R 8 and R 9 which are the same or different, are alkylene groups having carbon atoms of 2 to 6, more preferably, 2 to 3, and R 10 CO represents a residual group resulting from a fatty acid having carbon atoms of 8 to 30, more preferably, 12 to 24, from which a hydroxyl group has been excluded.
  • an alkyl group or a hydroxyalkyl group having carbon atoms of 1 to 3 is preferably used, and a methyl group, an ethyl group or a hydroxyethyl group is more preferably used.
  • a halogen ion such as a chloride ion, or an alkylsulfate ion derived from methylsulfate, ethylsulfate, etc. is preferably used.
  • the method for preparing the cationic surfactant that is is not particularly limited.
  • it can be prepared by quaternizing the product obtained by reacting an alkanol amine, an aminoalkyl amine or the like with an fatty acid or an ester thereof.
  • quaternary ammonium salt (I) examples thereof include: N-methyl-N,N,N-tri(long-chain alkanoyloxyethyl) ammonium salt, N-methyl-N,N-di(long-chain alkanoyloxyethyl)-N-long-chain alkanoylaminopropyl ammonium salt, N-methyl-N.N-di (long- chain alkanoyloxyethyl)-N-long-chain alkanoylaminoethyl ammonium salt, N-methyl-N,N-di(long-chain alkanoyloxyethyl)-N-long-chain alkyl ammonium sal t and N-methyl-tri-long-chain alkyl ammonium salt.
  • Those having the long-chain alkanoyloxy group and/or long-chain alkanoylamino group are preferably used because of its superior biodegradability.
  • the aprotic solvent used in the present invention is selected from the group of compounds represented by the formula (XII), and these may be liquid or solid matters at room temperature (25°C) as long as they are liquids at the time of the quaternizing process.
  • compounds represented by the formula (XII) are used since they have superior miscibility with water and also have preferable odor in the resulting quaternary ammonium salt.
  • the acyl group is preferably an acyl group derived from a long-chain fatty acid having carbon atoms of 8 to 30, more preferably, 12 to 24, such as tallow fatty acid, hydrogenated tallow fatty acid, palm stearic acid, hydrogenated palm stearic acid or a mixture of two or more kinds selected from these.
  • A is preferably prepared as an ethylene group or a propylene group, more preferably, an ethylene group.
  • n is preferably set to 1 to 30, more preferably, 5 to 30.
  • alkyl group the alkenyl group or the hydroxyalkyl group having carbon atoms of 1 to 6, represented by R 1 , R 2 and R 3
  • an alkyl group or a hydroxyalkyl group having carbon atoms of 1 to 3 is preferably used, and a methyl group, ethyl group or hydroxyethyl group is more preferably used.
  • the aprotic solvent is preferably used at 5 to 90 weight %, more preferably, 9 to 70 weight %, with respect to the tertiary amine.
  • the quaternizing agents used in the quaternizing reaction dimethylsulfate, diethylsulfate, methylchloride, etc. are listed.
  • the temperature at the time of the quaternizing reaction is preferably set to 30 to 150°C, more preferably, 50 to 120°C.
  • the solution when the compound represented by the formula (XII) is used as the aprotic solvent, the solution, as it is, without distilling the solvent may be applied to the softener.
  • quaternary ammonium salt obtained from the present invention those having a ratio of not less than 50 weight %, more preferably, not less than 85 weight %, most preferably, not less than 90 weight %, of the tri-long-chain alkyl component in the quaternary ammonium salts, are preferably used.
  • % represents weight reference unless otherwise defined.
  • Triethanol amine (149 g) and 821 g of hydrogenated tallow fatty acid were used and subjected to an esterification reaction at 200°C under nitrogen atmosphere for 10 hours to obtain N,N,N-tri (hydrogenated tallow alkanoyl oxyethyl) amine, and to this was further added 458 g of hexane, and this was subjected to a quaternizing reaction by using 126 g of dimethyl sulfate at 70°C for 10 hours. After the reaction, the solvent was evaporated therefrom under reduced pressure, and to this was then added 184 g of isopropanol to obtain an isopropanol solution of quaternary ammonium salt. Table 1 shows the quaternizing ratio and its composition.
  • the quaternizing ratio and compositions were measured by using an internal standard method based upon 1 H-NMR method by using MERCURY 400 made by VARIAN.
  • Table 1 shows the quaternizing ratio and its composition.
  • Table 1 shows the quaternizing ratio and its composition.
  • Table 1 shows the quaternizing ratio and its composition.
  • Table 1 shows the quaternizing ratio and its composition.
  • Table 1 shows the quaternizing ratio and its composition.
  • the solution of quaternary ammonium salt obtained in each of Examples 1 to 7 was taken in a manner so as to set the total of quaternary ammonium salt to 5 g, and after having been heated to 60°C, this was dripped into water at 60°C in a molten state to prepare 100 g of a softener composition.
  • the softness of these softener compositions was evaluated in the following methods. Table 2 shows the results of evaluation.
  • Triethanol amine (149 g) and 547 g of hydrogenated tallow fatty acid were used and subjected to an esterification reaction at 200°C under nitrogen atmosphere for 10 hours to obtain N,N-bis(hydrogenated tallow alkanoyl oxyethyl)-N-(2-hydroxyethyl) amine, and the same processes as Reference Example 1 were carried out by using 184 g of isopropanol as a quaternizing solvent to obtain an isopropanol solution of quaternary ammonium salt.
  • Table 1 shows the quaternizing ratio and its composition.
  • Triethanol amine (149 g) and 547 g of hydrogenated tallow fatty acid were used and subjected to an esterification reaction at 200°C under nitrogen atmosphere for 10 hours, and to this was added 139 g of isopropanol, and this was subjected to a quaternizing reaction at 60°C by using 126 g of dimethyl sulfate to obtain a propanol solution of N-methyl-N,N-bis (hydrogenated tallow alkanoyl oxyethyl)-N-(2-hydroxyethyl)ammonium methyl sulfate.
  • this solution had a long-chain alkyl quaternary ammonium salt content of 12 %, a di-long-chain alkyl quaternary ammonium salt content of 35 % and mono-long-chain alkyl quaternary ammonium salt content of 15 %.
  • Triethanol amine (149 g) and 547 g of hydrogenated tallow fatty acid were used and subjected to an esterification reaction at 200°C under nitrogen atmosphere for 10 hours to obtain N,N-bis(hydrogenated tallow alkanoyl oxyethyl)-N-(2-hydroxyethyl) amine, and the same processes as Reference Example 1 were carried out by using 330 g of hexane as a quaternizing solvent to obtain an isopropanol solution of quaternary ammonium salt.
  • Table 1 shows the quaternizing ratio and its composition.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (2)

  1. Verfahren zur Erzeugung von quaternären Ammoniumsalzen, dargestellt durch die folgende Formel (I), (II) oder (III), durch Reaktion eines tertiären Amins, dargestellt durch die folgende Formel (V), (VI) oder (VII), mit einem Quaternisierungsmittel, zur Herstellung von quaternären Ammoniumsalzen in zumindest einem aprotischen Lösungsmittel, ausgewählt aus Verbindungen, dargestellt durch die folgende Formel (XII):
    Figure imgb0023
    Figure imgb0024
    Figure imgb0025
     worin R1, R2 und R3 eine langkettige Alkyl- oder Alkenylgruppe mit einer Gesamtkohlenstoffatomzahl von 8 bis 40 sind, die gleich oder verschieden voneinander sein können und durch eine Ether-, Ester- oder Amidgruppe unterbrochen sein können; R4 eine Alkylgruppe, Alkenylgruppe oder Hydroxyalkylgruppe mit 1 bis 6 Kohlenstoffatomen ist, wobei mehrere R4 gleich oder verschieden voneinander sind und X- eine anionische Gruppe ist,
    Figure imgb0026
    Figure imgb0027
    Figure imgb0028
     worin R1, R2, R3 und R4 gleich sind wie oben beschrieben,

            R11O-(AO)n-R12     (XII)

    worin R11 und R12, die gleich oder verschieden voneinander sind, eine Alkylgruppe, Alkenylgruppe oder Acylgruppe jeweils mit 1 bis 30 Kohlenstoffatomen sind, A eine Alkylengruppe mit 2 bis 4 Kohlenstoffatomen ist, n eine Zahl von 1 bis 40 im Durchschnitt ist und die n-Gruppen A gleich oder verschieden voneinander sein können.
  2. Verfahren nach Anspruch 1, worin die Verbindung mit der Formel (XII) eine Verbindung mit der Formel (IV) ist:

            R5-COO-(AO)mR6     (IV)

    worin R5 eine Alkyl- oder Alkenylgruppe mit einer Gesamtkohlenstoffatomzahl von 7 bis 29 ist, R6 eine Alkyl- oder Alkenylgruppe mit 1 bis 6 Kohlenstoffatomen ist, A eine Alkylengruppe mit 2 bis 4 Kohlenstoffatomen ist und m eine Zahl von 1 bis 40 im Schnitt ist und mehrere Gruppen A gleich oder verschieden voneinander sein können.
EP07018604A 2001-03-08 2002-03-04 Verfahren zur Herstellung von quartären Ammoniumsalzen Expired - Lifetime EP1884560B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2001065091A JP4467821B2 (ja) 2001-03-08 2001-03-08 柔軟剤組成物
JP2001065090A JP4514975B2 (ja) 2001-03-08 2001-03-08 柔軟剤組成物
JP2001093069A JP4672164B2 (ja) 2001-03-28 2001-03-28 第４級アンモニウム塩の製法
EP02004360A EP1239024B1 (de) 2001-03-08 2002-03-04 Weichmacherzusammensetzung

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP02004360A Division EP1239024B1 (de) 2001-03-08 2002-03-04 Weichmacherzusammensetzung

Publications (3)

Publication Number Publication Date
EP1884560A2 EP1884560A2 (de) 2008-02-06
EP1884560A3 EP1884560A3 (de) 2008-02-27
EP1884560B1 true EP1884560B1 (de) 2010-02-10

Family

ID=27346194

Family Applications (2)

Application Number Title Priority Date Filing Date
EP07018604A Expired - Lifetime EP1884560B1 (de) 2001-03-08 2002-03-04 Verfahren zur Herstellung von quartären Ammoniumsalzen
EP02004360A Expired - Lifetime EP1239024B1 (de) 2001-03-08 2002-03-04 Weichmacherzusammensetzung

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP02004360A Expired - Lifetime EP1239024B1 (de) 2001-03-08 2002-03-04 Weichmacherzusammensetzung

Country Status (5)

Country Link
US (2) US6855682B2 (de)
EP (2) EP1884560B1 (de)
DE (2) DE60223614T2 (de)
ES (2) ES2294054T3 (de)
MX (1) MXPA02002549A (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4104894B2 (ja) * 2002-04-18 2008-06-18 花王株式会社 エステル基を有する第４級アンモニウム塩の製法
WO2003106605A1 (en) * 2002-06-13 2003-12-24 The Procter & Gamble Company Compositions comprising specfic fabric softener actives
ES2274142T3 (es) * 2003-06-24 2007-05-16 Cognis Ip Management Gmbh Preparacion acuosas de brillo perlado.
EP1909687A1 (de) 2005-07-13 2008-04-16 Boston Scientific Scimed, Inc. Einrast-schlingenankersysteme und relevante verfahren
GB0602741D0 (en) * 2006-02-10 2006-03-22 Unilever Plc Fabric conditioning compositions
US20100197560A1 (en) * 2006-02-10 2010-08-05 Nepras Marshall J Fabric Conditioning Active Compositions
DE102006009973A1 (de) * 2006-03-03 2007-09-06 Cognis Ip Management Gmbh Bei Raumtemperatur flüssige Verbindungen
JP5394215B2 (ja) 2008-12-11 2014-01-22 花王株式会社 柔軟剤組成物
CN102775818B (zh) * 2012-08-06 2013-10-30 上海梵和聚合材料有限公司 含有改性水滑石成分的洗涤颗粒组成和方法
MX360843B (es) 2012-12-11 2018-11-20 Colgate Palmolive Co Composicion de esterquat que tiene un alto contenido de triesterquat.
US9476012B2 (en) 2012-12-11 2016-10-25 Colgate-Palmolive Company Esterquat composition having high triesterquat content
CN103409991A (zh) * 2013-07-18 2013-11-27 吴江市利达上光制品有限公司 一种衣物抗菌柔顺剂的制备方法
EP3359515B1 (de) 2015-10-07 2019-12-18 Elementis Specialties, Inc. Netz- und antischaummittel
EP3181667A1 (de) 2015-12-18 2017-06-21 Kao Corporation, S.A. Weichspülerwirkstoffzusammensetzungen
PT3418354T (pt) 2017-06-20 2020-07-07 Kao Corp Sa Composições de substâncias ativas amaciadoras de tecidos
EP3418355B1 (de) 2017-06-20 2020-06-03 Kao Corporation, S.A. Weichspülerwirkstoffzusammensetzungen
EP3418353B1 (de) 2017-06-20 2020-08-26 Kao Corporation, S.A. Weichspülerwirkstoffzusammensetzungen
BR112020025672A2 (pt) * 2018-06-26 2021-03-16 Evonik Operations Gmbh Processo para produzir um composto de amônio quaternário e um material amaciante de tecido, bem como material e produto amaciante de tecido

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1935499A1 (de) 1969-07-12 1971-01-14 Basf Ag Avivagemittel
NL7706714A (nl) * 1976-06-23 1977-12-28 Hoechst Ag Quaternaire ammoniumverbindingen, werkwijzen voor haar bereiding en haar toepassing in zachtmakende spoelmiddelen voor de was.
GB1567947A (en) * 1976-07-02 1980-05-21 Unilever Ltd Esters of quaternised amino-alcohols for treating fabrics
GB2041967B (en) * 1977-12-23 1982-12-15 Procter & Gamble Laundry detergent substrate articles
DE3126522A1 (de) * 1981-07-04 1983-01-20 Basf Ag, 6700 Ludwigshafen Quaternaere ammoniumsalze und verfahren zu ihrer herstellung
FR2574400B1 (fr) * 1984-12-12 1988-05-20 Interox Composes organiques d'ammonium quaternaire et procede pour leur fabrication
JPS6369884A (ja) * 1986-09-12 1988-03-29 Lion Corp 柔軟剤組成物
ES2021900A6 (es) 1989-07-17 1991-11-16 Pulcra Sa Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester.
JPH03118358A (ja) * 1989-09-29 1991-05-20 Mitsubishi Kasei Corp 第４級アンモニウム・エチルサルフェートの製造法
DE4015849A1 (de) * 1990-05-17 1991-11-21 Henkel Kgaa Quaternierte ester
DE4243701A1 (de) 1992-12-23 1994-06-30 Henkel Kgaa Wäßrige Textilweichmacher-Dispersionen
JP3357453B2 (ja) * 1993-09-10 2002-12-16 花王株式会社 液体柔軟仕上剤組成物並びに新規第４級アンモニウム塩並びに該塩の製造法
WO1996003370A1 (fr) * 1994-07-27 1996-02-08 Kao Corporation Composition pour adoucissant liquide et sel d'ammonium quaternaire
EP1445303A3 (de) * 1994-10-14 2004-10-20 Kao Corporation Flüssige Weichspülerzusammensetzung
DE4437032A1 (de) * 1994-10-17 1996-04-18 Henkel Kgaa Textile Weichmacher-Konzentrate
JPH09255988A (ja) * 1996-03-22 1997-09-30 Lion Corp 液体洗浄剤組成物
US5916863A (en) 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
CN1085724C (zh) * 1996-05-31 2002-05-29 阿克佐诺贝尔公司 制备包含季酯铵化合物和脂肪酸的固体组合物的方法
CA2310612A1 (en) * 1997-11-24 1999-06-03 The Procter & Gamble Company Clear or translucent aqueous fabric softener compositions containing high electrolyte content and optional phase stabilizer
US6268332B1 (en) * 1997-11-24 2001-07-31 The Procter & Gamble Company Low solvent rinse-added fabric softners having increased softness benefits
DE19904233A1 (de) * 1999-02-03 2000-08-10 Clariant Gmbh Feste Vormischung für Wäscheweichspülmittel
JP4024438B2 (ja) 1999-11-01 2007-12-19 花王株式会社 第４級アンモニウム塩組成物

Also Published As

Publication number Publication date
DE60223614D1 (de) 2008-01-03
DE60223614T2 (de) 2009-07-09
ES2294054T3 (es) 2008-04-01
EP1239024A3 (de) 2003-07-16
ES2340078T3 (es) 2010-05-28
US6855682B2 (en) 2005-02-15
EP1884560A2 (de) 2008-02-06
US7115779B2 (en) 2006-10-03
US20030036499A1 (en) 2003-02-20
DE60235331D1 (de) 2010-03-25
EP1239024A2 (de) 2002-09-11
US20050107634A1 (en) 2005-05-19
MXPA02002549A (es) 2005-07-25
EP1884560A3 (de) 2008-02-27
EP1239024B1 (de) 2007-11-21

Similar Documents

Publication Publication Date Title
EP1884560B1 (de) Verfahren zur Herstellung von quartären Ammoniumsalzen
CA2384317C (en) Quaternary ammonium salt composition
FI89605B (fi) Stabila bionedbrytbara mjukgoeringsmedel foer tyger, vilka innehaoller lineaera alkoxilerade alkoholer
EP0721936B1 (de) Flüssige weichmacher und quaternäre ammoniumsalze
JPH07138876A (ja) 液体柔軟仕上剤組成物並びに新規第４級アンモニウム塩並びに該塩の製造法
EP1103650B2 (de) Weichmacherzusammensetzung
EP0707059A2 (de) Flüssige Weichspülerzusammensetzung, ihre Verwendung und Verfahren zur Herstellung eines quaternären Ammoniumsalzes
US6624137B1 (en) Softening finish composition
JP4672164B2 (ja) 第４級アンモニウム塩の製法
WO2003027057A1 (en) Method for preparing of cationic surfactants and fabric softener composition using the same
JPH09137379A (ja) 柔軟仕上剤組成物
EP1096055B1 (de) Weichmacherzusammensetzung
JP4467821B2 (ja) 柔軟剤組成物
JPH08301822A (ja) 新規な第４級アンモニウム塩及びそれを含有する柔軟剤組成物
JPH07102479A (ja) 液体柔軟仕上剤組成物
JP3827867B2 (ja) 柔軟仕上げ剤組成物
JP2003519293A (ja) アルコキシレート化添加剤を含有する透明な軟化用調合物
JP5154634B2 (ja) 第４級アンモニウム塩組成物及び柔軟剤組成物
JP3502684B2 (ja) 液体柔軟仕上剤組成物及び新規第４級アンモニウム塩
JP4514975B2 (ja) 柔軟剤組成物
WO2000058429A1 (en) Use of an alkyl polyglycoside to enhance the performance of a cationic fabric care product
JPH0657632A (ja) 柔軟仕上剤
JPH0921068A (ja) 液体柔軟仕上剤組成物
JPH06101172A (ja) 新規アミン誘導体及びこれを含有する液体柔軟仕上剤組成物
CA2129707A1 (en) Biodegradable fabric softening composition

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AC Divisional application: reference to earlier application

Ref document number: 1239024

Country of ref document: EP

Kind code of ref document: P

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): DE ES FR GB

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): DE ES FR GB

17P Request for examination filed

Effective date: 20080428

AKX Designation fees paid

Designated state(s): DE ES FR GB

17Q First examination report despatched

Effective date: 20081218

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AC Divisional application: reference to earlier application

Ref document number: 1239024

Country of ref document: EP

Kind code of ref document: P

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE ES FR GB

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REF Corresponds to:

Ref document number: 60235331

Country of ref document: DE

Date of ref document: 20100325

Kind code of ref document: P

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2340078

Country of ref document: ES

Kind code of ref document: T3

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20101111

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 14

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20160302

Year of fee payment: 15

Ref country code: ES

Payment date: 20160211

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20160208

Year of fee payment: 15

Ref country code: GB

Payment date: 20160302

Year of fee payment: 15

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 60235331

Country of ref document: DE

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20170304

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20171130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20170331

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20171003

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20170304

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20180629

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20170305